Well, after years of visiting Dimensions and finding interest in weight-gain stories--not the unnatural ones but the romantic stories with a realistic flair. I have found a woman interested in participating in the lifestyle, a lifestyle I was, and still am, hesitant to join in on fully.

She is 5'7" with a starting weight of 357lbs but currently weighs in at 405lbs. She says her limit is 550lbs.

So, I know, what's my question. Has anyone else here really participated in a feedee/feeder relationship? And if so, what was your experience? What are the advantages and disadvantages? What are the roadblocks? Any suggestions? Do you have any regrets? And, by the way, a feedee or feeder can answer any or all questiosn.

You want replys? Okay, you'll get a replay however I've never been in one of those relationships so you're only going to get some assumptions based on what I expect and what I know from other individual's experiences.
So, here goes.

First off, it depends on the relationship. There are some relationships which are primarily sexual while others are much more emotional. Assuming there is a connection beyond weight it will not be as sexual as some feeder/feedee or BBW/FA relationships. If you don't have anything that bonds you with this person beyond the weight gain my own question is to ask why are you even with them? If there's nothing beyond the weight gain the relationship will be primarily based around the fetish and it will most likely tank. Most relationships that are only based around sex and fetishism kinda go like that.

Some roadblocks are ofcourse the issues that the women might end up with due to weight gain. Not everybody takes weight gain the same. While some people may have confidence issues others might have health issues so you shouldn't assume that she will reach the weight limit of 550. There are others who may also get somewhat addicted to it and decide to go over their limit you must expect that to also be a possibility as well. Let's also not forget that if there's weight gain involved....there's going to be money issues. You need to make sure that there is enough money to keep on the weight gain as well ofcourse clothing and you need to make sure your lover is comfortable, caring for an SSBBW will be no easy task.

There, that is some of the issues which may prop up.
Just some, there are likely more but meh.

Well then good, because from what I am aware of those relationships tend to get ruined when they're based only on the fetish (then again that speaks for most relationships, they're ruined when it's only a sexual thing).

Honestly, I think sharing something like this with someone you care about can really enhance the relationship.

However just be prepared for what I have mentioned before and other issues.

It sounds like you have the right attitude and are not only in it for the feedee/feeder thing so I say why not.

Go for it, you have the right approach about it so there shouldn't be too many problems.

Been there, did that, screwed it up horribly (surprisingly enough it wasn't a weight-related gaffe). There weren't any disadvantages or roadblocks and my only regrets were, as I said, not feeding related. I say go for it, be yourself, and communicate 'cause that's really important.

...I have found a woman interested in participating in the lifestyle, a lifestyle I was, and still am, hesitant to join in on fully....

I think you have your answer right there: if you are hesitant, then you need more time to think things through. Simply indulging a partner by participating in something you're not comfortable with, on any level, is never a good idea and will almost always come back to haunt you.

I would echo what has been said about if there is any hesitancy at all you should wait until you are ready to commit to the lifestyle. That being said you should also keep in mind that unlike other lifestyles such as becoming a vegan or such the feeder/feedee lifestyle takes two people so even if you do get over your hesitancy and decide to commit be ready for the whole thing to end abruptly if your partner changes her mind. Forgive if I'm not making any sense since I'm trying to keep it brief, but in my experience that's usually the reason the lifestyle comes to an end is one person has a change of heart and that change of heart usually comes not on the same schedule as the other person involved.

It just helps to know that going in. Might save a messy ending if you keep it in the back of your head and keep the lines of communication open at all stages of the relationship.